Selective Postsynthetic Reduction of Pyridinium Hydrazone Cages

Logan A.V. Faulkner; Rosemary J. Goodwin; Katarina Trajković; Bailee R. Smith; Annie L. Colebatch; Nicholas G. White

doi:10.1021/acs.orglett.6c01271

Selective Postsynthetic Reduction of Pyridinium Hydrazone Cages

Logan A.V. Faulkner
, Rosemary J. Goodwin
, Katarina Trajković
, Bailee R. Smith
, Annie L. Colebatch
, Nicholas G. White^*

^*Corresponding author for this work

Research output: Contribution to journal › Letter › peer-review

Abstract

Postsynthetic modification of a series of hexacationic organic cages containing pyridinium and hydrazone groups gave a new family of neutral organic cages through a high-yielding single-step reduction reaction. The reaction selectively reduces all six pyridinium rings to 1,2,3,6-tetrahydropyridines but leaves the hydrazone C═N bond untouched. The neutral cages display strong sulfate binding to give cage·(SO₄^2–)₂ complexes in DMSO.

Original language	English
Pages (from-to)	6032-6036
Number of pages	5
Journal	Organic Letters
Volume	28
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.6c01271
Publication status	Published - 15 May 2026

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title = "Selective Postsynthetic Reduction of Pyridinium Hydrazone Cages",

abstract = "Postsynthetic modification of a series of hexacationic organic cages containing pyridinium and hydrazone groups gave a new family of neutral organic cages through a high-yielding single-step reduction reaction. The reaction selectively reduces all six pyridinium rings to 1,2,3,6-tetrahydropyridines but leaves the hydrazone C═N bond untouched. The neutral cages display strong sulfate binding to give cage·(SO42–)2 complexes in DMSO.",

author = "Faulkner, \{Logan A.V.\} and Goodwin, \{Rosemary J.\} and Katarina Trajkovi{\'c} and Smith, \{Bailee R.\} and Colebatch, \{Annie L.\} and White, \{Nicholas G.\}",

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doi = "10.1021/acs.orglett.6c01271",

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TY - JOUR

T1 - Selective Postsynthetic Reduction of Pyridinium Hydrazone Cages

AU - Faulkner, Logan A.V.

AU - Goodwin, Rosemary J.

AU - Trajković, Katarina

AU - Smith, Bailee R.

AU - Colebatch, Annie L.

AU - White, Nicholas G.

PY - 2026/5/15

Y1 - 2026/5/15

N2 - Postsynthetic modification of a series of hexacationic organic cages containing pyridinium and hydrazone groups gave a new family of neutral organic cages through a high-yielding single-step reduction reaction. The reaction selectively reduces all six pyridinium rings to 1,2,3,6-tetrahydropyridines but leaves the hydrazone C═N bond untouched. The neutral cages display strong sulfate binding to give cage·(SO42–)2 complexes in DMSO.

AB - Postsynthetic modification of a series of hexacationic organic cages containing pyridinium and hydrazone groups gave a new family of neutral organic cages through a high-yielding single-step reduction reaction. The reaction selectively reduces all six pyridinium rings to 1,2,3,6-tetrahydropyridines but leaves the hydrazone C═N bond untouched. The neutral cages display strong sulfate binding to give cage·(SO42–)2 complexes in DMSO.

UR - https://www.scopus.com/pages/publications/105039116155

U2 - 10.1021/acs.orglett.6c01271

DO - 10.1021/acs.orglett.6c01271

M3 - Letter

C2 - 42065371

AN - SCOPUS:105039116155

SN - 1523-7060

VL - 28

SP - 6032

EP - 6036

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Selective Postsynthetic Reduction of Pyridinium Hydrazone Cages

Abstract

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